Hydrochloric Acid → 4-fluoro-N-(4-(5-oxo-3, 5,6,10b-tetrahydro-2H-oxazolo[3,2-c]pyrido[3,2-e]pyrimidin-10-ylamino)phenyl)-2-(trifluoromethyl)benzamide

HRID 1045489Notes

Reaction equation

HRID 1045489 reaction equation
Cl[C:2]1[C:7]2[CH:8]3[O:15][CH2:14][CH2:13][N:9]3[C:10](=[O:12])[NH:11][C:6]=2[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:36])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]([F:35])([F:34])[F:33])=[CH:19][CH:18]=1.Cl.O1CCOCC1>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:2]3[C:7]4[CH:8]5[O:15][CH2:14][CH2:13][N:9]5[C:10](=[O:12])[NH:11][C:6]=4[N:5]=[CH:4][CH:3]=3)=[CH:22][CH:21]=2)=[O:36])=[C:26]([C:32]([F:33])([F:34])[F:35])[CH:27]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 44603462N-(4-Aminophenyl)-4-fluoro-2-trifluoromethyl-benzamideHCID 70498679HCID 70498679, compound

Product 1

HCID 704980424-fluoro-N-(4-(5-oxo-3, 5,6,10b-tetrahydro-2H-oxazolo[3,2-c]pyrido[3,2-e]pyrimidin-10-ylamino)phenyl)-2-(trifluoromethyl)benzamide

Procedure

42 (16 mg, 0.07 mmol), N-(4-aminophenyl)-4-fluoro-2-(trifluoromethyl) benzamide (22 mg, 0.07 mmol), and 4.0M HCl in dioxane (18 μl, 0.07 mmol) were suspended in a sealed tube, and placed in microwave at 140° C. for 1 h. The crude product was purified directly via HPLC to provide 43. LC-MS (M+H=488, obsd.=488).

Workup

  1. customThe crude product was purified directly via HPLC

Sources & evidence

ORD record
ord-007376d335dc4a8891589c5bdfb48683
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

Loading…